Lots of discussion about $30k houses that rent for $700 in the rust belt and OK.  

In all honesty, once you close on the deal and get some experience under your belt, you will likely begin to regret aspects of the deal and discover you could have improved certain things.

If you already have one property under your belt, the scariest step is already taken ;) You're in the best possible place to learn from people of all experience levels and specialties, so take advantage of it! 

Now that I have my first purchase under my belt, I think I’m ready for a more involved project where I can add value. 

So if you're determined to only look in one specific area, then you have to roll with the punches.If you can't get a deal under your belt for better than the going rate, then at least, make sure that rate works!

I am fine with rehabbing and holding a rental as well, and after I get a few of those under my belt, I may consider flipping.I have owned two very old houses in the area and remodeled both pretty much from top to bottom, just put in the second new bathroom in my current residence.

I'm researching and it seems like a belt sander + 24 grit is going to get the paint off with some time and patience. 

Jeremy, this is what people that aren't from the Midwest/Great Lakes/"Rust Belt" don't realize: Even though you'll still have "declining population", it doesn't mean that Cleveland is a cesspool.

Once you get 5-10 deals under your belt then you can use those as case studies and pitch decks to investors

I have one real estate investment property under my belt, which I recently sold.Purchased it in 2019 and did a full rehab on the first floor.